Cedrus

Windstar Cruises · Philipsburg round trip

Classic Caribbean

Choose this for small Caribbean harbours and a week with time to enjoy the deck.

Your whole cruise journey, taken care of.

From packing advice and your airport ride to flights, hotels, port transfers and cruise check-in. We plan the details around your time on the water.

We help with documents, registration, dining and shore-experience booking windows, disembarkation and the journey home.

A tropical coast and clear blue water
Ocean View Stateroom aboard Wind Surf; illustrative category image
Illustrative category; layout and outlook vary by cabin. · Windstar Cruises
Ocean View Suite aboard Wind Surf; illustrative category image
Illustrative category; layout and outlook vary by cabin. · Windstar Cruises
Your time
7 nights8 calendar days · Wind Surf
Your route
Philipsburg round trip
When to go
Jan 9 – 16, 2027
Cruise fare reference
From $3,027USD per person, two sharing · cruise onlySee fare basis & inclusions
  • Winter island-hopping aboard a five-masted yacht.
  • Wind Surf
  • 7 nights aboard

Ashore & aboard

Your journey,
day by day.

Choose a cabin, then follow the published route below. We help you arrange your time ashore around the ship’s schedule.

Published from $3,027USD per person · 2 sharingOceanview lead-in; exact category to confirm

iCruise published USD reference per person for two sharing, including taxes and fees. This is an independent retailer’s fare, not a confirmed CEDRUS or Coastline quote. Exact category and fare eligibility require confirmation.

Price source · Checked Oct 30, 2026. Subject to change.

The cruise fare covers the sailing only. Flights, pre/post hotels and transfers are quoted separately unless expressly included. See the included and additional arrangements below the cabins.

7 nights aboard

Your cabin on Wind Surf

Wind Surf is a sail-assisted Windstar yacht. Sails and engines are both used; the captain and conditions determine time under sail. These yachts offer ocean-view cabins rather than private balcony cabins. Compare cabin position, stairs and the specific layout before choosing.

Cabins & suites to consider

Choose your favorite
Ocean View Stateroom aboard Wind Surf; illustrative category image
Illustrative category; layout and outlook vary by cabin. · Windstar Cruises

Ocean View Stateroom

An ocean-facing cabin with portholes, for travelers who expect to spend most of the day ashore or on deck.

  • 188 sq ft
  • Queen or twin beds
  • No private balcony

Cabin fare confirmed in your quote.

Choose a preference; we confirm the exact cabin, fare and availability before booking.

Explore the details
Ocean View Suite aboard Wind Surf; illustrative category image
Illustrative category; layout and outlook vary by cabin. · Windstar Cruises

Ocean View Suite

More living space with a sitting area and two bathrooms.

  • 376 sq ft
  • Ocean view
  • No private balcony

Cabin fare confirmed in your quote.

Choose a preference; we confirm the exact cabin, fare and availability before booking.

Explore the details
Included & quoted separately
  • Included: Your selected stateroom and onboard dining
  • Included: Use of the watersports platform when operating
  • Plan separately: Excursions, flights, hotels and transfers
  • Plan separately: Beverage packages, Wi-Fi and gratuities unless included in your selected fare

Day 1 · Jan 9

Philipsburg, St. Maarten

Embark in St. Maarten. Embarkation day: arrive in the departure city in advance; we coordinate your hotel-to-ship transfer around check-in.

Day 2 · Jan 10

At sea

Time aboard the yacht.

Day 3 · Jan 11

Terre-de-Haut

Les Saintes harbour.

Day 4 · Jan 12

Mayreau

A small Grenadines island.

Day 5 · Jan 13

Roseau

Dominica’s green interior.

Day 6 · Jan 14

Basseterre

St. Kitts and its heritage.

Day 7 · Jan 15

Gustavia

The harbour of St. Barts.

Day 8 · Jan 16

Philipsburg, St. Maarten

Embark in St. Maarten. Disembarkation morning. Onward flights and transfers must leave time for formalities and the journey from the port.

One journey, from your door

Before & after the cruise

Before boarding, quoted separately: Arrive at least a day ahead; we can arrange a hotel and the transfer to the confirmed embarkation point.

After the cruise, quoted separately: We coordinate disembarkation, any onward stay and your airport transfer around your actual flight.

Flights, hotels, transfers, packing guidance and check-in support can be coordinated as one journey. Cruise fares do not automatically include those arrangements.

Planning details & sources

A thoughtfully arranged journey

  • Tendering, stairs and sea conditions affect access. The operator may revise ports and timings; we confirm the final schedule and fare before booking.
  • Port order and schedules can change. Map pins show port locations; connections are illustrative, not the ship’s navigational track. Shore activities are quoted separately unless expressly included.
  • Before boarding, quoted separately: Arrive at least a day ahead; we can arrange a hotel and the transfer to the confirmed embarkation point.
  • After the cruise, quoted separately: We coordinate disembarkation, any onward stay and your airport transfer around your actual flight.
  • Flights, hotels, transfers, packing guidance and check-in support can be coordinated as one journey. Cruise fares do not automatically include those arrangements.

Explore the places behind the journey

Published itineraryShip, cabins & deck planFare inclusionsPublished price reference

A few favorites. A personal journey.

Your journey,
taking shape.

0 cabins · 0 experiences you love

Choose what catches your eye, or let us guide you from here.

Published from $3,027USD per person · 2 sharingOceanview lead-in; exact category to confirmPrice source · Checked Oct 30, 2026. Subject to change.
Make this journey yoursCompare other departure dates

Your favorites help us shape Philipsburg round trip around you. Cabins, availability and the final itinerary are confirmed with your travel designer.